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Carbenium Ions in Substitution Reactions at the Amino Nitrogen Atom

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Abstract

Tropylium, xanthylium, and tritylium salts characterized by different stabilities differently reacted with biologically active amines. The reactions of tropylium perchlorate and tetrafluoroborate with 4-(cyclohepta-2,4,6-trien-1-yl)aniline was accompanied by hydrolysis of the N-(cyclohepta-2,4,6-trien-1-yl) derivative, the N-xanthenyl derivative underwent dehydrogenation, whereas tritylium perchlorate failed to react with 4-(cyclohepta-2,4,6-trien-1-yl)aniline. The reactions of pyrimidin-2-amine with tropylium, xanthylium, and tritylium salts afforded products of substitution of one hydrogen atom in the amino group with high yields. The N-substituted pyrimidin-2-amine derivatives were stable, and neither their dehydrogenation nor hydrolysis was observed.

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Authors and Affiliations

  1. Pryanishnikov Perm State Agro-Technological University, ul. Petropavlovskaya 23, Perm, 614990, Russia

    L. P. Yunnikova & V. V. Esenbaeva

Authors
  1. L. P. Yunnikova
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  2. V. V. Esenbaeva
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Correspondence to L. P. Yunnikova.

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Original Russian Text © L.P. Yunnikova, V.V. Esenbaeva, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 7, pp. 1015–1018.

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Yunnikova, L.P., Esenbaeva, V.V. Carbenium Ions in Substitution Reactions at the Amino Nitrogen Atom. Russ J Org Chem 54, 1018–1022 (2018). https://doi.org/10.1134/S1070428018070084

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